32 Chestnut St, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$2,913,900

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 4,167 sqft (on 0.46 acres)

32 Chestnut St, Wellesley, MA 02481

Est. Refi. Payment $17,378/mo*
Refinance Your Home
Currently Off Market - Sold Apr 5, 2019 for $1,960,000

Home Value

Trulia Estimate
$2.91M
Since last month
Decreased$52K (-1.7%)
Since last year
Increased$93K (+3.3%)
Since last sale
Increased$954K (+48.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +65% in the last 10 years
MonthEstimated value
2026
August 2026$2.91M
July 2026$2.97M
June 2026$2.96M
May 2026$2.97M
April 2026$2.92M
March 2026$2.91M
February 2026$2.79M
January 2026$2.76M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Garden Rd, Wellesley, MA
0.19
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
7 Garden Rd, Wellesley, MA
0.21
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
40 Chestnut St, Wellesley, MA
0.04
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
7 Cliff Rd, Wellesley, MA
0.23
Single-Family Home
$1,865,000
04/02/26
5
3.5
3,774
54 Colburn Rd, Wellesley, MA
0.27
Single-Family Home
$1,655,000
01/30/26
4
2.5
2,204
92 Woodlawn Ave, Wellesley, MA
0.33
Single-Family Home
$1,953,000
06/03/26
4
2.5
2,627
35 Arnold Rd, Wellesley, MA
0.42
Single-Family Home
$2,525,000
06/26/26
4
3.5
3,497
26 Edmunds Rd, Wellesley, MA
0.39
Single-Family Home
$3,115,000
01/09/26
4
3.5
4,294
4 Arnold Rd, Wellesley, MA
0.53
Single-Family Home
$1,750,000
09/23/25
4
2.5
3,156
21 Elm St, Wellesley, MA
0.48
Single-Family Home
$2,690,000
07/16/26
4
3.5
4,761

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
40 Chestnut St, Wellesley, MA 02481
0.04
$2,450,000
5
3.5
3,369
Recently Sold
46 Garden Rd, Wellesley, MA 02481
0.08
$3,555,400
4
4.5
4,636
Off Market
37 Garden Rd, Wellesley, MA 02481
0.11
$3,137,900
6
4.5
4,297
Off Market
20 Colburn Rd, Wellesley, MA 02481
0.13
$2,247,100
3
2.5
3,184
Off Market
10 Lanark Rd, Wellesley, MA 02481
0.14
$4,400,000
6
3.5
7,404
Recently Sold
63 Garden Rd #C1, Wellesley, MA 02481
0.15
$1,903,200
2
2
1,643
Off Market
63 Garden Rd #C4, Wellesley, MA 02481
0.15
$2,186,600
3
2
2,326
Off Market
63 Garden Rd #G7, Wellesley, MA 02481
0.15
-
3
2
2,342
Off Market
17 Colburn Rd, Wellesley, MA 02481
0.15
$1,851,500
3
1.5
1,878
Off Market
63 Garden Rd #C5, Wellesley, MA 02481
0.16
$995,000
1
1.5
1,205
For Sale
63 Garden Rd #G2, Wellesley, MA 02481
0.16
$1,100,000
2
2
1,224
Recently Sold
21 Cushing Rd, Wellesley, MA 02481
0.13
$3,814,100
5
5
4,558
Off Market

Local Information

  • Map ViewExplore the area around 32 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1895
Lot Size
0.46 acres
Living Area
4,167 sqft
Price/Sqft
$699

About this House

Renowned as one of Wellesley's most picturesque streets with its dazzling array of eclectic architectural styles, Chestnut St. now offers up a real treasure- the rarely marketed Carriage House at # 32. Built in 1895 as part of the Albion Robert Clapp Estate, this fine residence combines charm with modern amenities. The state of the art upgraded kitchen- Wolf stove with grill, Sub-Zero refrigerator, oversized hood, plus 3 sinks- features cherry cabinets and island with honed black granite countertops. Adjacent is a wetbar with wine fridge plus Sub-Zero refrigerator drawers. A dramatic two-story library has a caramel colored pine, beadboard ceiling plus a view into the second floor loft space. An oversized (25 ft. long) master bedroom plus three other generous size bedrooms grace this home. There is a newly installed heating/cooling system. Lush outdoor gardens and space on the half acre grounds. A unique residence where you will smile every time you turn into the driveway. Welcome Home!
32 Chestnut St, Wellesley, MA 02481 is a 4 bedroom, 3 bathroom, 4,167 sqft single-family home built in 1895. It last sold for $1,960,000 on Apr 5, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,913,900, with a rent estimate of $7,449/month.

Home Details for 32 Chestnut St

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 11Types of Rooms: Dining Room, Family Room, Laundry Room, Library, Office, PantryStorage
Heating & Cooling
Heating: Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood, Slate
Appliances & Utilities
DishwasherDryerRefrigerator
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Stone, BrickFoundation Type: Crawl RaisedGardenPatioPorchSprinkler System
Parking & Garage
Parking Spaces: 3

Property Information

Year Built
Year Built: 1895Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Apr 5, 2019
Source: N/A
Sold
$1,960,000
Feb 11, 2019
Source: Agent Provided
Pending
$2,200,000
Jan 29, 2019
Source: Agent Provided
Listed For Sale
$2,200,000
Apr 1, 2012
Source: Agent Provided
ListingRemoved
$1,550,000
Dec 20, 2011
Source: Agent Provided
Listed For Sale
$1,550,000

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

Around this home

What Locals Say about Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
    Flag
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 32 Chestnut St

  • What is 32 Chestnut St estimated to be worth?
    Trulia's estimated value for 32 Chestnut St in Wellesley, MA is $2,913,900.
  • What is the price history for 32 Chestnut St?
    32 Chestnut St in Wellesley, MA last sold for $1,960,000 in April 2019.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 32 Chestnut St have air conditioning?
    Yes, 32 Chestnut St in Wellesley, MA has air conditioning.
  • Does 32 Chestnut St have laundry facilities?
    Yes, 32 Chestnut St in Wellesley, MA has laundry facilities.

Explore by feature - Pet Friendly

16 pet-friendly rentals in Wellesley, MA

Explore by feature - Garage

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Explore by feature - Air Conditioning

24 rentals with air conditioning in Wellesley, MA

Explore by feature - Washer/dryer

28 rentals with a washer/dryer in Wellesley, MA

Explore by feature - Outdoor Space

7 rentals with an outdoor space in Wellesley, MA

Apartments for Rent

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Off Market Homes Near 32 Chestnut St

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